Friday’s MLB draft signing deadline came and went at 5 p.m. EST with the Houston Astros and 2014 No. 1 overall pick Brady Aiken unable to reach a deal.

It is just the third time in MLB draft history that the top pick hasn’t signed.

Things got ugly between the Astros and the high school senior from San Diego after the two sides reportedly agreed on a $6.5 million signing bonus days after the draft in June. But a physical came back that gave Houston some cause for concern.

The medical exam revealed that the left-hander had an issue with his elbow ligament, leading the Astros to lower their offer to around $3.1 million.

Aiken’s agent, Casey Close, wasn’t a fan of how the Astros handled the situation, publicly criticizing the organization for how they handled the negotiations. Tony Clark of the MLBPA also weighed in on the matter, saying he was “disappointed” in Houston’s dealing of the Aiken situation.

The Astros were willing to increase their offer to nearly $5 million — still $1.5 million less than their original offer — Jon Heyman of CBS Sports reports, but it wasn’t enough.

“We tried to engage Casey Close three times today … there was no interest,” Houston general manager Jeff Luhnow told the Houston Chronicle on Friday.

To make matters worse for Houston, they also failed to reach agreements with fifth-round pick Jacob Nix and 21st-rounder Mac Marshall. But because the Astros were unable to sign the No. 1 overall selection, they will receive the No. 2 pick in the 2015 MLB draft as compensation.

Aiken will likely now attend UCLA next season — where both he and Nix are committed — but he won’t be eligible for the draft until 2017.